title: From β-amino-γ-sultone to unusual bicyclic pyridine and pyrazine heterocyclic systems: synthesis and cytostatic and antiviral activities.
abstract: Herein we describe the first successful application of the β-amino-γ-sultone system as an intermediate for the synthesis of hitherto virtually unknown 3H-[1,2]-oxathiole [4,3-b]pyridine and pyrazine 1,1-dioxide bicyclic heterocyclic systems. All novel compounds were evaluated for their antiviral and cytostatic activities. Compounds 3 a, 15 a, and 21 a inhibited HIV-1-induced cytopathicity. Compound 7 showed remarkable cytostatic activity, and can be regarded as a potential antitumor candidate for further exploration.
authors.affiliation: Instituto de Química Médica (C.S.I.C.), Juan de la Cierva 3, 28006 Madrid, Spain.
authors.forename: Sonia
authors.initials: S
authors.lastname: de Castro
authors.forename: Olga
authors.initials: O
authors.lastname: Familiar
authors.forename: Graciela
authors.initials: G
authors.lastname: Andrei
authors.forename: Robert
authors.initials: R
authors.lastname: Snoeck
authors.forename: Jan
authors.initials: J
authors.lastname: Balzarini
authors.forename: María-José
authors.initials: MJ
authors.lastname: Camarasa
authors.forename: Sonsoles
authors.initials: S
authors.lastname: Velázquez
mesh_terms: D000588:Amines / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002478:Cells, Cultured; D054697:Cytostatic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015658:HIV Infections / Q000188:drug therapy / Q000378:metabolism / Q000473:pathology; D015497:HIV-1 / Q000187:drug effects*; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011719:Pyrazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013450:Sulfones / Q000737:chemistry; D014779:Virus Replication / Q000187:drug effects
chemical_list: D000588:Amines; D000998:Antiviral Agents; D054697:Cytostatic Agents; D006574:Heterocyclic Compounds, 2-Ring; D011719:Pyrazines; D011725:Pyridines; D013450:Sulfones